4-[(1S,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]butanoic acid

ID: ALA2368480

PubChem CID: 73354399

Max Phase: Preclinical

Molecular Formula: C19H30O6

Molecular Weight: 354.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@@H](CCCC(=O)O)O[C@@H]2O[C@]3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3

Standard InChI:  InChI=1S/C19H30O6/c1-11-7-8-14-12(2)15(5-4-6-16(20)21)22-17-19(14)13(11)9-10-18(3,23-17)24-25-19/h11-15,17H,4-10H2,1-3H3,(H,20,21)/t11-,12-,13+,14+,15-,17-,18+,19-/m1/s1

Standard InChI Key:  WEWYKNVABULCLM-WGCHMBTQSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
   -0.5742  -16.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2314  -16.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461  -16.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983  -17.7362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745  -16.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825  -17.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2958  -16.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5895  -16.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5630  -17.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8567  -17.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454  -17.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1343  -18.6515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8407  -19.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582  -18.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016  -15.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2338  -16.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293  -17.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408  -17.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2703  -19.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310  -19.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1103  -20.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006  -21.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6201  -21.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312  -21.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298  -22.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6097  -18.4869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228  -18.3594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626  -15.6099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  0
  1  2  1  0
  8 15  1  6
  5  8  1  0
  9  6  1  0
  6  7  1  0
  3 16  1  0
  7  8  1  0
 10 17  1  6
 16 17  1  0
  9 10  1  0
  3 18  1  1
  3  4  1  0
 11  4  1  0
 14 19  1  1
  5 10  1  0
 13 20  1  1
  5  2  1  0
 20 21  1  0
 21 22  1  0
  1  3  1  0
 22 23  1  0
  9 14  1  0
 23 25  1  0
 10 11  1  0
 11 12  1  0
 23 24  2  0
 11 26  1  1
  9 27  1  6
  5 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2368480

   4-[(1S,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]butanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 354.44

Molecular Weight (Monoisotopic): 354.2042

AlogP: 3.49

#Rotatable Bonds: 4

Polar Surface Area: 74.22

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.99

CX Basic pKa: ┄

CX LogP: 3.82

CX LogD: 0.66

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: 3.15

References

1. Jung M, Tak J, Chung WY, Park KK..  (2006)  Antiangiogenic activity of deoxoartemisinin derivatives on chorioallantoic membrane.,  16  (5): [PMID:16380253] [10.1016/j.bmcl.2005.11.074]

Source

Source(1):

• Scientific Literature